Diisopropylethylamine → 1-Cyclopentyl-5-(3-difluoromethyl-phenyl)-6-methyl-4-oxo-1,4-dihydro-pyridine-3-carboxylic acid (5-methyl-[1,3,4]oxadiazol-2-ylmethyl)-amide

HRID 524345Notes

Reaction equation

HRID 524345 reaction equation
[CH:1]1([N:6]2[C:11]([CH3:12])=[C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([CH:19]([F:21])[F:20])[CH:14]=3)[C:9](=[O:22])[C:8]([C:23](O)=[O:24])=[CH:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[CH3:59][C:60]1[O:64][C:63]([CH2:65][NH2:66])=[N:62][N:61]=1>CN(C=O)C>[CH3:59][C:60]1[O:64][C:63]([CH2:65][NH:66][C:23]([C:8]2[C:9](=[O:22])[C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([CH:19]([F:20])[F:21])[CH:14]=3)=[C:11]([CH3:12])[N:6]([CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5]3)[CH:7]=2)=[O:24])=[N:62][N:61]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 14442192[(5-Methyl-1,3,4-oxadiazol-2-yl)methyl]amineHCID 867115981-Cyclopentyl-5-(3-difluoromethyl-phenyl)-6-methyl-4-oxo-1,4-dihydro-pyridine-3-carboxylic acid

Product 1

HCID 867115971-Cyclopentyl-5-(3-difluoromethyl-phenyl)-6-methyl-4-oxo-1,4-dihydro-pyridine-3-carboxylic acid (5-methyl-[1,3,4]oxadiazol-2-ylmethyl)-amide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1-cyclopentyl-5-(3-difluoromethyl-phenyl)-6-methyl-4-oxo-1,4-dihydro-pyridine-3-carboxylic acid (preparation 9, 116 mg, 0.334 mmol), HBTU (140 mg, 0.369 mmol), DIPEA (116 μL, 0.668 mmol) in DMF (1 mL) is stirred for 15 min at room temperature. C-(5-methyl-1,3,4-oxadiazol-2-yl)-methylamine (46 mg, 0.407 mmol) is added and the reaction mixture is stirred for 72 h at room temperature. The reaction mixture is purified by preparative reversed-phase HPLC (XBridge, gradient of methanol in water, 0.3% NH4OH, 60° C.). Yield: 67 mg (45% of theory); ESI mass spectrum: [M+H]+=443; Retention time HPLC: 0.98 min (Z003_001).

Workup

  1. customThe reaction mixture is purified by preparative reversed-phase HPLC (XBridge, gradient of methanol in water, 0.3% NH4OH, 60° C.)
  2. custom0.98 min (Z003_001)

Sources & evidence

ORD record
ord-ad35590c9a13430ba2fef428a610bf14
Source dataset
uspto-grants-2016_05
Patent number
US09340507B2

Reaction notes

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